3-(4-Fluoro­phen­yl)-6-meth­oxy-2-(4-pyrid­yl)quinoxaline

Jahns, H.; Koch, P.; Schollmeyer, D.; Laufer, S.

doi:10.1107/S1600536809022119

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 7| July 2009| Page o1626

doi:10.1107/S1600536809022119

Open

access

3-(4-Fluorophenyl)-6-methoxy-2-(4-pyridyl)quinoxaline

Hartmut Jahns,^a Pierre Koch,^a Dieter Schollmeyer ^b and Stefan Laufer ^a ^*

^aInstitute of Pharmacy, Department of Pharmaceutical and Medicinal Chemistry, Eberhard-Karls-University Tübingen, Auf der Morgenstelle 8, 72076 Tübingen, Germany, and ^bDepartment of Organic Chemistry, Johannes Gutenberg-University Mainz, Duesbergweg 10-14, D-55099 Mainz, Germany
^*Correspondence e-mail: stefan.laufer@uni-tuebingen.de

(Received 13 May 2009; accepted 10 June 2009; online 20 June 2009)

In the title compound, C₂₀H₁₄FN₃O, the quinoxaline system makes dihedral angles of 32.38 (7) and 48.04 (7)° with the 4-fluorophenyl and pyridine rings, respectively. The 4-fluorophenyl ring makes a dihedral angle of 57.77 (9)° with the pyridine ring. In the crystal, the molecules form dimeric C—H⋯N hydrogen-bonded R₂²(20) ring motifs lying about crystallographic inversion centers. The dimeric units stack via π–π interactions between methoxyphenyl rings and pyridine–fluorophenyl rings with centroid–centroid distances of 3.720 (1) and 3.823 (1) Å, respectively. The respective average perpendicular distances are 3.421 and 3.378 Å, with dihedral angles between the rings of 1.31 (9) and 11.64 (9)°.

Related literature

Many chinoxaline derivatives have been prepared and their biological activity have been studied, see: He et al. (2003 ); Kim et al. (2004 ). For intermolecular C—H⋯N hydrogen bonds, see: Taylor & Kennard (1982 ). For distinct ring motifs formed via O—H⋯N hydrogen bonds, see: Habib & Janiak (2008 ); Friščič & MacGillivray (2003 ). For graph-set notation, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₂₀H₁₄FN₃O
M_r = 331.34
Orthorhombic, P b c a
a = 7.3886 (4) Å
b = 12.2071 (8) Å
c = 34.562 (6) Å
V = 3117.3 (6) Å³
Z = 8
Cu Kα radiation
μ = 0.80 mm⁻¹
T = 193 K
0.45 × 0.22 × 0.13 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: none
2950 measured reflections
2950 independent reflections
2542 reflections with I > 2σ(I)
3 standard reflections frequency: 60 min intensity decay: 2%

Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.124
S = 1.05
2950 reflections
228 parameters
H-atom parameters constrained
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C15—H15⋯N21ⁱ	0.95	2.44	3.368 (3)	165
Symmetry code: (i) -x, -y, -z+1.

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ); cell refinement: CAD-4 Software; data reduction: CORINC (Dräger & Gattow, 1971 ); program(s) used to solve structure: SIR97 (Altomare et al., 1999 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: PLATON (Spek, 2009 ); software used to prepare material for publication: PLATON.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809022119/si2176sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809022119/si2176Isup2.hkl

checkCIF report

Comment top

Functionalized quinoxaline derivatives are well known in pharmaceutical industry. They have been shown to possess antibacterial activity (Kim et al. 2004) and as PDGF-R tyrosine kinase inhibitors (He et al. 2003).

The title compound, (I), was prepared in the course of our studies on 2-(2-alkylaminopyridin-4-yl)-3-(4-fluorophenyl)quinoxalines as potent p38 mitogen-activated protein (MAP) kinase inhibitors. The two molecules of I are connected into a centrosymmetric dimer by intermolecular C15–H15···N21 hydrogen bonds [graph set R₂²(20) (Bernstein et al. 1995)] (Fig.1 and Table 1). By searching the CCDC a similar O—H···N hydrogen bond pattern could be found in the structure EHOTUQ (Friščič & MacGillivray 2003), with a R₄⁴(46) ring system. A variety of distinct ring motifs formed via hydrogen bonded donors and acceptors (O—H···O, O—H···N) has been described for the 4/1/2 adduct of benzene-1,3,5-tricarboxylic acid, 1,2-bis(1,2,4-triazol-4-yl)ethane and water by Habib & Janiak (2008). The C—H···N hydrogen bond of the title compound (Table 1) confirms the hydrogen-bond geometry values reviewed by Taylor & Kennard (1982), where the C—H···N distances vary between 2.523 Å and 2.721 Å, and the angles around the H atom range between 124.6° and 157.3°. The quinoxaline ring makes dihedral angles of 32.38 (7)° and 48.04 (7)° to the 4-fluorophenyl ring and the pyridine ring, respectively. The 4-fluorophenyl ring makes dihedral angles of 57.77 (9)° with the pyridine ring.

π—π interactions between the pyridin rings and the 4-fluorophenyl rings along the b axis have Cg2···Cg4ⁱⁱ distances of 3.823 (1) Å, and the distances between Cg3···Cg3ⁱⁱⁱ of the methoxyphenyl rings are 3.720 (1) Å along the a axis (Fig. 2). The respective average perpendicular stacking distances are 3.378 Å and 3.421 Å, with dihedral angles between the rings 1.31° and 11.64°. Symmetry codes ii = 1/2 - x, 1/2 + y, z; iii = -1/2 + x y, 3/2 - z. Cg2, Cg3 and Cg4 are the centroids of rings N21, C20, C19, C18, C23, C22; C4 - C9; and C11 - C16.

Related literature top

Many chinoxaline derivatives have been prepared and their biological activity have been studied, see: He et al. (2003); Kim et al. (2004). For intermolecular C—H···N hydrogen bonds, see: Taylor & Kennard (1982). For distinct ring motifs formed via O—H···N hydrogen bonds, see: Habib & Janiak (2008); Friščič & MacGillivray (2003). For graph-set notation, see: Bernstein et al. (1995).

Experimental top

The title compound I was prepared by irradiating 1-(4-fluorophenyl)-2-(pyridin-4-yl)ethane-1,2-dion (137 mg, 0.6 mmol), o-phenylendiamine (82 mg, 0.6 mmol) and methanol-acetic acid (9:1, 6 ml) in a sealed tube at 433 K for 5 min by moderating the initial microwave power (250 W). After the mixture was cooled to room temperature in a stream of compressed air, the solvent was removed under reduced pressure and the residue was purified by flash chromatography (silica gel, from petroleum ether/ ethyl acetate 2:1 to 1:2) to yield 82 mg of I. Crystals suitable for X-ray analysis were obtained by slow crystallization from diethylether/n-hexane.

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software (Enraf–Nonius, 1989); data reduction: CORINC (Dräger & Gattow, 1971); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top

	Fig. 1. View of the centrosymmetric dimer of I. Displacement ellipsoids are drawn at the 50% probability level. H atoms are depicted as circles of arbitrary size. Hydrogen bonds with dashed lines. Symmetry code a: -x, -y, 1-z.
	Fig. 2. A section of the crystal structure of the title compound, viewed along the b axis. Aromatic rings involved in π—π stacking interactions are shown in red and blue. Hydrogen bonds with dashed lines.

3-(4-Fluorophenyl)-6-methoxy-2-(4-pyridyl)quinoxaline top

Crystal data top

C₂₀H₁₄FN₃O	F(000) = 1376
M_r = 331.34	D_x = 1.412 Mg m⁻³
Orthorhombic, Pbca	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 25 reflections
a = 7.3886 (4) Å	θ = 61–69°
b = 12.2071 (8) Å	µ = 0.80 mm⁻¹
c = 34.562 (6) Å	T = 193 K
V = 3117.3 (6) Å³	Plate, colourless
Z = 8	0.45 × 0.22 × 0.13 mm

Data collection top

Enraf–Nonius CAD-4 diffractometer	R_int = 0.000
Radiation source: FR571 rotating anode	θ_max = 70.1°, θ_min = 2.6°
Graphite monochromator	h = 0→8
ω/2θ scans	k = 0→14
2950 measured reflections	l = 0→42
2950 independent reflections	3 standard reflections every 60 min
2542 reflections with I > 2σ(I)	intensity decay: 2%

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.044	H-atom parameters constrained
wR(F²) = 0.124	w = 1/[σ²(F_o²) + (0.063P)² + 1.8096P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max < 0.001
2950 reflections	Δρ_max = 0.32 e Å⁻³
228 parameters	Δρ_min = −0.24 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0024 (2)

Crystal data top

C₂₀H₁₄FN₃O	V = 3117.3 (6) Å³
M_r = 331.34	Z = 8
Orthorhombic, Pbca	Cu Kα radiation
a = 7.3886 (4) Å	µ = 0.80 mm⁻¹
b = 12.2071 (8) Å	T = 193 K
c = 34.562 (6) Å	0.45 × 0.22 × 0.13 mm

Data collection top

Enraf–Nonius CAD-4 diffractometer	R_int = 0.000
2950 measured reflections	3 standard reflections every 60 min
2950 independent reflections	intensity decay: 2%
2542 reflections with I > 2σ(I)

Refinement top

R[F² > 2σ(F²)] = 0.044	0 restraints
wR(F²) = 0.124	H-atom parameters constrained
S = 1.05	Δρ_max = 0.32 e Å⁻³
2950 reflections	Δρ_min = −0.24 e Å⁻³
228 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.0332 (2)	0.08992 (13)	0.65003 (5)	0.0212 (4)
C2	0.1240 (2)	−0.01069 (13)	0.64015 (5)	0.0234 (4)
N3	0.1695 (2)	−0.08283 (11)	0.66708 (4)	0.0248 (3)
C4	0.1415 (2)	−0.05500 (14)	0.70477 (5)	0.0241 (4)
C5	0.1912 (2)	−0.12816 (15)	0.73464 (5)	0.0280 (4)
H5	0.2383	−0.1984	0.7284	0.034*
C6	0.1717 (3)	−0.09798 (15)	0.77228 (5)	0.0290 (4)
H6	0.2040	−0.1478	0.7922	0.035*
C7	0.1034 (2)	0.00738 (15)	0.78208 (5)	0.0257 (4)
C8	0.0529 (2)	0.07962 (14)	0.75376 (5)	0.0253 (4)
H8	0.0074	0.1499	0.7604	0.030*
C9	0.0691 (2)	0.04866 (14)	0.71462 (5)	0.0224 (4)
N10	0.01133 (19)	0.11909 (11)	0.68664 (4)	0.0228 (3)
C11	−0.0457 (2)	0.16507 (13)	0.62087 (5)	0.0214 (4)
C12	−0.0501 (2)	0.27756 (14)	0.62867 (5)	0.0240 (4)
H12	0.0020	0.3047	0.6519	0.029*
C13	−0.1297 (3)	0.34958 (14)	0.60292 (5)	0.0277 (4)
H13	−0.1341	0.4258	0.6084	0.033*
C14	−0.2026 (2)	0.30841 (15)	0.56913 (5)	0.0277 (4)
C15	−0.2047 (3)	0.19825 (15)	0.56049 (5)	0.0286 (4)
H15	−0.2590	0.1720	0.5374	0.034*
C16	−0.1249 (2)	0.12698 (14)	0.58669 (5)	0.0258 (4)
H16	−0.1240	0.0507	0.5813	0.031*
F17	−0.27461 (17)	0.37943 (9)	0.54317 (3)	0.0401 (3)
C18	0.1841 (2)	−0.03833 (14)	0.60030 (5)	0.0239 (4)
C19	0.1592 (3)	−0.14261 (14)	0.58520 (5)	0.0286 (4)
H19	0.0981	−0.1973	0.5998	0.034*
C20	0.2249 (3)	−0.16553 (15)	0.54863 (5)	0.0340 (4)
H20	0.2038	−0.2367	0.5385	0.041*
N21	0.3161 (2)	−0.09438 (13)	0.52658 (5)	0.0344 (4)
C22	0.3408 (3)	0.00561 (15)	0.54154 (5)	0.0317 (4)
H22	0.4053	0.0580	0.5266	0.038*
C23	0.2776 (2)	0.03680 (14)	0.57757 (5)	0.0272 (4)
H23	0.2979	0.1091	0.5867	0.033*
O24	0.09436 (18)	0.02718 (11)	0.82084 (3)	0.0324 (3)
C25	0.0370 (3)	0.13400 (17)	0.83218 (6)	0.0356 (5)
H25A	0.1183	0.1888	0.8209	0.053*
H25B	0.0400	0.1398	0.8605	0.053*
H25C	−0.0866	0.1468	0.8230	0.053*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0199 (8)	0.0226 (8)	0.0211 (8)	−0.0022 (6)	0.0009 (6)	−0.0003 (6)
C2	0.0229 (8)	0.0223 (8)	0.0248 (8)	−0.0015 (7)	0.0009 (7)	0.0012 (6)
N3	0.0253 (7)	0.0243 (7)	0.0249 (7)	0.0000 (6)	0.0026 (6)	0.0024 (6)
C4	0.0201 (8)	0.0264 (8)	0.0259 (8)	−0.0007 (7)	0.0018 (6)	0.0031 (7)
C5	0.0270 (9)	0.0260 (8)	0.0311 (9)	0.0018 (7)	0.0026 (7)	0.0058 (7)
C6	0.0267 (9)	0.0313 (9)	0.0289 (9)	0.0013 (8)	−0.0004 (7)	0.0100 (7)
C7	0.0207 (8)	0.0355 (10)	0.0209 (8)	−0.0039 (7)	0.0012 (7)	0.0049 (7)
C8	0.0237 (8)	0.0265 (8)	0.0257 (8)	−0.0004 (7)	0.0014 (7)	0.0011 (7)
C9	0.0184 (8)	0.0254 (8)	0.0234 (8)	−0.0022 (7)	0.0004 (6)	0.0038 (7)
N10	0.0225 (7)	0.0237 (7)	0.0221 (7)	−0.0001 (6)	0.0002 (6)	0.0013 (6)
C11	0.0195 (8)	0.0225 (8)	0.0220 (8)	−0.0002 (6)	0.0024 (6)	−0.0002 (6)
C12	0.0225 (8)	0.0248 (8)	0.0246 (8)	−0.0003 (6)	0.0000 (7)	−0.0019 (7)
C13	0.0293 (9)	0.0226 (8)	0.0312 (9)	0.0019 (7)	0.0014 (7)	−0.0001 (7)
C14	0.0258 (9)	0.0310 (9)	0.0263 (9)	0.0045 (7)	−0.0004 (7)	0.0068 (7)
C15	0.0283 (10)	0.0354 (9)	0.0221 (8)	0.0011 (8)	−0.0029 (7)	−0.0020 (7)
C16	0.0258 (9)	0.0245 (8)	0.0272 (8)	−0.0004 (7)	0.0006 (7)	−0.0031 (7)
F17	0.0459 (7)	0.0397 (6)	0.0347 (6)	0.0119 (5)	−0.0078 (5)	0.0092 (5)
C18	0.0219 (8)	0.0235 (8)	0.0262 (9)	0.0030 (7)	−0.0012 (7)	0.0001 (7)
C19	0.0318 (10)	0.0241 (9)	0.0300 (9)	−0.0010 (7)	0.0004 (8)	0.0014 (7)
C20	0.0444 (12)	0.0253 (9)	0.0323 (9)	−0.0019 (8)	−0.0002 (9)	−0.0058 (8)
N21	0.0429 (10)	0.0319 (8)	0.0284 (8)	0.0021 (7)	0.0025 (7)	−0.0039 (7)
C22	0.0369 (11)	0.0293 (9)	0.0288 (9)	−0.0010 (8)	0.0053 (8)	0.0017 (7)
C23	0.0303 (9)	0.0228 (8)	0.0284 (9)	−0.0008 (7)	0.0011 (7)	−0.0022 (7)
O24	0.0350 (7)	0.0406 (8)	0.0216 (6)	0.0003 (6)	−0.0003 (5)	0.0052 (5)
C25	0.0353 (11)	0.0436 (11)	0.0279 (9)	0.0009 (9)	0.0001 (8)	−0.0011 (8)

Geometric parameters (Å, º) top

C1—N10	1.324 (2)	C13—C14	1.381 (3)
C1—C2	1.440 (2)	C13—H13	0.9500
C1—C11	1.482 (2)	C14—F17	1.356 (2)
C2—N3	1.325 (2)	C14—C15	1.378 (3)
C2—C18	1.486 (2)	C15—C16	1.387 (2)
N3—C4	1.362 (2)	C15—H15	0.9500
C4—C5	1.414 (2)	C16—H16	0.9500
C4—C9	1.416 (2)	C18—C19	1.388 (2)
C5—C6	1.360 (3)	C18—C23	1.391 (2)
C5—H5	0.9500	C19—C20	1.382 (3)
C6—C7	1.423 (3)	C19—H19	0.9500
C6—H6	0.9500	C20—N21	1.338 (3)
C7—O24	1.363 (2)	C20—H20	0.9500
C7—C8	1.369 (2)	N21—C22	1.338 (2)
C8—C9	1.410 (2)	C22—C23	1.384 (3)
C8—H8	0.9500	C22—H22	0.9500
C9—N10	1.363 (2)	C23—H23	0.9500
C11—C16	1.398 (2)	O24—C25	1.426 (2)
C11—C12	1.400 (2)	C25—H25A	0.9800
C12—C13	1.382 (2)	C25—H25B	0.9800
C12—H12	0.9500	C25—H25C	0.9800

N10—C1—C2	120.82 (15)	C12—C13—H13	120.7
N10—C1—C11	115.80 (15)	F17—C14—C15	118.43 (16)
C2—C1—C11	123.35 (15)	F17—C14—C13	118.67 (16)
N3—C2—C1	121.23 (15)	C15—C14—C13	122.89 (16)
N3—C2—C18	115.13 (15)	C14—C15—C16	117.77 (17)
C1—C2—C18	123.52 (15)	C14—C15—H15	121.1
C2—N3—C4	117.89 (15)	C16—C15—H15	121.1
N3—C4—C5	120.10 (16)	C15—C16—C11	121.39 (16)
N3—C4—C9	120.69 (15)	C15—C16—H16	119.3
C5—C4—C9	119.16 (16)	C11—C16—H16	119.3
C6—C5—C4	120.00 (17)	C19—C18—C23	117.26 (16)
C6—C5—H5	120.0	C19—C18—C2	121.15 (16)
C4—C5—H5	120.0	C23—C18—C2	121.47 (15)
C5—C6—C7	120.69 (16)	C20—C19—C18	118.88 (17)
C5—C6—H6	119.7	C20—C19—H19	120.6
C7—C6—H6	119.7	C18—C19—H19	120.6
O24—C7—C8	125.10 (17)	N21—C20—C19	124.49 (17)
O24—C7—C6	114.32 (15)	N21—C20—H20	117.8
C8—C7—C6	120.58 (16)	C19—C20—H20	117.8
C7—C8—C9	119.36 (16)	C20—N21—C22	116.18 (16)
C7—C8—H8	120.3	N21—C22—C23	123.54 (17)
C9—C8—H8	120.3	N21—C22—H22	118.2
N10—C9—C8	119.04 (15)	C23—C22—H22	118.2
N10—C9—C4	120.78 (15)	C22—C23—C18	119.64 (16)
C8—C9—C4	120.17 (15)	C22—C23—H23	120.2
C1—N10—C9	118.06 (15)	C18—C23—H23	120.2
C16—C11—C12	118.64 (16)	C7—O24—C25	116.56 (14)
C16—C11—C1	122.23 (15)	O24—C25—H25A	109.5
C12—C11—C1	119.03 (15)	O24—C25—H25B	109.5
C13—C12—C11	120.66 (16)	H25A—C25—H25B	109.5
C13—C12—H12	119.7	O24—C25—H25C	109.5
C11—C12—H12	119.7	H25A—C25—H25C	109.5
C14—C13—C12	118.61 (16)	H25B—C25—H25C	109.5
C14—C13—H13	120.7

N10—C1—C2—N3	7.9 (3)	N10—C1—C11—C12	32.8 (2)
C11—C1—C2—N3	−170.22 (16)	C2—C1—C11—C12	−149.01 (16)
N10—C1—C2—C18	−167.94 (16)	C16—C11—C12—C13	−0.6 (3)
C11—C1—C2—C18	13.9 (3)	C1—C11—C12—C13	−177.19 (16)
C1—C2—N3—C4	−5.4 (2)	C11—C12—C13—C14	−0.8 (3)
C18—C2—N3—C4	170.78 (15)	C12—C13—C14—F17	−177.56 (16)
C2—N3—C4—C5	−178.67 (16)	C12—C13—C14—C15	2.1 (3)
C2—N3—C4—C9	−1.1 (2)	F17—C14—C15—C16	177.79 (16)
N3—C4—C5—C6	176.67 (16)	C13—C14—C15—C16	−1.9 (3)
C9—C4—C5—C6	−1.0 (3)	C14—C15—C16—C11	0.4 (3)
C4—C5—C6—C7	−0.7 (3)	C12—C11—C16—C15	0.8 (3)
C5—C6—C7—O24	−178.82 (16)	C1—C11—C16—C15	177.30 (16)
C5—C6—C7—C8	1.2 (3)	N3—C2—C18—C19	46.7 (2)
O24—C7—C8—C9	−179.94 (15)	C1—C2—C18—C19	−137.24 (18)
C6—C7—C8—C9	0.0 (3)	N3—C2—C18—C23	−129.12 (18)
C7—C8—C9—N10	177.21 (16)	C1—C2—C18—C23	47.0 (3)
C7—C8—C9—C4	−1.7 (3)	C23—C18—C19—C20	−1.1 (3)
N3—C4—C9—N10	5.7 (3)	C2—C18—C19—C20	−177.09 (17)
C5—C4—C9—N10	−176.72 (16)	C18—C19—C20—N21	1.7 (3)
N3—C4—C9—C8	−175.42 (15)	C19—C20—N21—C22	−1.0 (3)
C5—C4—C9—C8	2.2 (3)	C20—N21—C22—C23	−0.1 (3)
C2—C1—N10—C9	−3.2 (2)	N21—C22—C23—C18	0.6 (3)
C11—C1—N10—C9	175.05 (14)	C19—C18—C23—C22	0.1 (3)
C8—C9—N10—C1	177.83 (15)	C2—C18—C23—C22	176.04 (17)
C4—C9—N10—C1	−3.2 (2)	C8—C7—O24—C25	−3.7 (3)
N10—C1—C11—C16	−143.69 (17)	C6—C7—O24—C25	176.37 (16)
C2—C1—C11—C16	34.5 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15···N21ⁱ	0.95	2.44	3.368 (3)	165

Symmetry code: (i) −x, −y, −z+1.

Experimental details

Crystal data
Chemical formula	C₂₀H₁₄FN₃O
M_r	331.34
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	193
a, b, c (Å)	7.3886 (4), 12.2071 (8), 34.562 (6)
V (Å³)	3117.3 (6)
Z	8
Radiation type	Cu Kα
µ (mm⁻¹)	0.80
Crystal size (mm)	0.45 × 0.22 × 0.13

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	2950, 2950, 2542
R_int	0.000
(sin θ/λ)_max (Å⁻¹)	0.610

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.124, 1.05
No. of reflections	2950
No. of parameters	228
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.32, −0.24

Computer programs: CAD-4 Software (Enraf–Nonius, 1989), CORINC (Dräger & Gattow, 1971), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15···N21ⁱ	0.95	2.44	3.368 (3)	165

Symmetry code: (i) −x, −y, −z+1.

References

Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115–119. Web of Science CrossRef CAS IUCr Journals Google Scholar
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Dräger, M. & Gattow, G. (1971). Acta Chem. Scand. 25, 761–762. Google Scholar
Enraf–Nonius (1989). CAD-4 Software. Enraf–Nonius, Delft, The Netherlands. Google Scholar
Friščič, T. & MacGillivray, L. R. (2003). Chem. Commun. pp. 1306–1307. Google Scholar
Habib, H. A. & Janiak, C. (2008). Acta Cryst. E64, o1199. Web of Science CSD CrossRef IUCr Journals Google Scholar
He, W., Myers, M. R., Hanney, B., Spada, A. P., Bilder, G., Galzcinski, H., Amin, D., Needle, S., Page, K., Jayyosi, Z. & Perrone, M. H. (2003). Bioorg. Med. Chem. Lett. 13, 3097–3100. Web of Science CrossRef PubMed CAS Google Scholar
Kim, Y. B., Kim, Y. H., Park, J. Y. & Kim, S. K. (2004). Bioorg. Med. Chem. Lett. 14, 541–544. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Taylor, R. & Kennard, O. (1982). J. Am. Chem. Soc. 104, 5063–5070. CrossRef CAS Web of Science Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 7| July 2009| Page o1626

doi:10.1107/S1600536809022119

Open

access